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Ammonium Chloride → (4R,5S,6S)-1,1-diisopropoxy-5-hydroxy-2,2,4,6-tetramethyl-8-nonen-3-one

HRID 348235
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 348235
C([O:4][CH:5]([O:13][CH:14]([CH3:16])[CH3:15])[C:6]([CH3:12])([CH3:11])[C:7](=[O:10])[CH2:8][CH3:9])(C)C.C([N-][CH:21]([CH3:23])[CH3:22])(C)C.[Li+].[CH3:25][C@@H:26]([CH2:29][CH:30]=[CH2:31])[CH:27]=[O:28].[NH4+].[Cl-]>C1COCC1.C(Cl)Cl>[CH:14]([O:13][CH:5]([O:4][CH:21]([CH3:22])[CH3:23])[C:6]([CH3:11])([CH3:12])[C:7](=[O:10])[C@H:8]([CH3:9])[C@@H:27]([OH:28])[C@@H:26]([CH3:25])[CH2:29][CH:30]=[CH2:31])([CH3:15])[CH3:16]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 10176097(2S)-2-methyl-4-pentenalHCID 113221791,1-Diisopropoxy-2,2-dimethyl-3-pentanone

Produkt 1

HCID 11198250(4R,5S,6S)-1,1-diisopropoxy-5-hydroxy-2,2,4,6-tetramethyl-8-nonen-3-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344
Dichloromethane
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A solution of 1,1-diisopropoxy-2,2-dimethyl-3-pentanone (3.29 g) in 15 mL of THF is added slowly to a solution of lithium diisopropylamide (15.7 mmol) in 20 mL of THF cooled to −78° C., the mixture is stirred for 30 minutes, warmed to −40° C. and stirred for 30 minutes, then recooled to −78° C. A solution of (2S)-2-methyl-4-pentenal (16.36 mmol) in 2 mL of CH2Cl2 is added and the mixture is stirred for 1 hour at −78° C. Saturated aq. NH4Cl is added and the mixture is warmed to ambient temperature and extracted with ethyl acetate. The extract is dried over Na2SO4, filtered, and evaporated. The residue is purified by silica gel chromatography (2% ethyl acetate/hexanes) to separate the two diastereomeric products.

Aufarbeitung

  1. temperaturewarmed to −40° C.
  2. stirringstirred for 30 minutes
  3. customrecooled to −78° C
  4. stirringthe mixture is stirred for 1 hour at −78° C
  5. temperaturethe mixture is warmed to ambient temperature
  6. extractionextracted with ethyl acetate
  7. dry with materialThe extract is dried over Na2SO4
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue is purified by silica gel chromatography (2% ethyl acetate/hexanes)
  11. customto separate the two diastereomeric products

Quellen und Nachweise

ORD-Eintrag
ord-c2dea00e9c53444ba8aa14cf3a136fbe
Quelldatensatz
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07176235B2

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